(1R,2R,4S,12R,13S,16E)-13-hydroxy-25-(6-hydroxy-9H-pyrido[3,4-b]indol-1-yl)-11,22-diazapentacyclo[11.11.2.12,22.02,12.04,11]heptacosa-16,25-dien-7-one

Details

• Internal ID: 1c19ea5a-a172-4601-ae83-d628e434845a
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: (1R,2R,4S,12R,13S,16E)-13-hydroxy-25-(6-hydroxy-9H-pyrido[3,4-b]indol-1-yl)-11,22-diazapentacyclo[11.11.2.12,22.02,12.04,11]heptacosa-16,25-dien-7-one
• SMILES (Canonical): C1CCN2CCC3C(=CC(CCC=CC1)(C4C3(C2)CC5N4CCCC(=O)CC5)O)C6=NC=CC7=C6NC8=C7C=C(C=C8)O
• SMILES (Isomeric): C1CCN2CC[C@H]3C(=C[C@@](CC/C=C/C1)([C@H]4[C@]3(C2)C[C@H]5N4CCCC(=O)CC5)O)C6=NC=CC7=C6NC8=C7C=C(C=C8)O
• InChI: InChI=1S/C36H44N4O3/c41-25-8-7-18-40-24(9-10-25)21-35-23-39-17-6-4-2-1-3-5-15-36(43,34(35)40)22-29(30(35)14-19-39)32-33-27(13-16-37-32)28-20-26(42)11-12-31(28)38-33/h1,3,11-13,16,20,22,24,30,34,38,42-43H,2,4-10,14-15,17-19,21,23H2/b3-1+/t24-,30-,34+,35-,36-/m0/s1
• InChI Key: GNVMYASVHYRDQY-FTXQUYPASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₄N₄O₃
• Molecular Weight: 580.80 g/mol
• Exact Mass: 580.34134128 g/mol
• Topological Polar Surface Area (TPSA): 92.70 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 5.96
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	-	0.8625	86.25%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8482	84.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8499	84.99%
OATP1B3 inhibitior	+	0.9433	94.33%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.9958	99.58%
P-glycoprotein inhibitior	+	0.8651	86.51%
P-glycoprotein substrate	+	0.7980	79.80%
CYP3A4 substrate	+	0.7201	72.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7233	72.33%
CYP3A4 inhibition	-	0.5083	50.83%
CYP2C9 inhibition	-	0.7850	78.50%
CYP2C19 inhibition	-	0.7831	78.31%
CYP2D6 inhibition	-	0.7247	72.47%
CYP1A2 inhibition	-	0.6984	69.84%
CYP2C8 inhibition	+	0.7557	75.57%
CYP inhibitory promiscuity	-	0.6410	64.10%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6037	60.37%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9482	94.82%
Skin irritation	-	0.7459	74.59%
Skin corrosion	-	0.9327	93.27%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6360	63.60%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8346	83.46%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8476	84.76%
Acute Oral Toxicity (c)	III	0.5737	57.37%
Estrogen receptor binding	+	0.7960	79.60%
Androgen receptor binding	+	0.7905	79.05%
Thyroid receptor binding	+	0.5407	54.07%
Glucocorticoid receptor binding	+	0.6534	65.34%
Aromatase binding	+	0.5801	58.01%
PPAR gamma	+	0.6436	64.36%
Honey bee toxicity	-	0.7832	78.32%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.6932	69.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.51%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.15%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.93%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.89%	89.00%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	96.54%	96.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.26%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.82%	92.94%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	93.75%	91.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.20%	99.23%
CHEMBL5103	Q969S8	Histone deacetylase 10	91.57%	90.08%
CHEMBL5203	P33316	dUTP pyrophosphatase	91.45%	99.18%
CHEMBL213	P08588	Beta-1 adrenergic receptor	91.30%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	91.26%	93.04%
CHEMBL2581	P07339	Cathepsin D	91.03%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.01%	95.56%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	89.70%	93.10%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	89.33%	96.00%
CHEMBL1937	Q92769	Histone deacetylase 2	89.21%	94.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.50%	94.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	88.35%	96.39%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.17%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.85%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.65%	95.89%
CHEMBL3310	Q96DB2	Histone deacetylase 11	86.73%	88.56%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	86.49%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.18%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.06%	97.25%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	85.32%	90.24%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.98%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.12%	86.33%
CHEMBL4208	P20618	Proteasome component C5	83.26%	90.00%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	82.50%	85.49%
CHEMBL1951	P21397	Monoamine oxidase A	81.95%	91.49%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.85%	94.08%
CHEMBL255	P29275	Adenosine A2b receptor	80.15%	98.59%
CHEMBL2535	P11166	Glucose transporter	80.10%	98.75%
CHEMBL3384	Q16512	Protein kinase N1	80.01%	80.71%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162902368
• LOTUS: LTS0065657
• wikiData: Q105013381